Water → HCID 66942140, compound

HRID 536643Notes

Reaction equation

HRID 536643 reaction equation
C([O:3][C:4]([C:6]1[C:11]2[CH2:12][C@@H:13]3[C:18]([CH3:20])([CH3:19])[C@:17]([CH3:21])([C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH2:16][CH2:15][N:14]3[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>O1CCCC1>[CH2:22]([N:14]1[CH2:15][CH2:16][C@:17]2([CH3:21])[C:18]([CH3:20])([CH3:19])[C@H:13]1[CH2:12][C:11]1[C:6]([CH2:4][OH:3])=[CH:7][CH:8]=[CH:9][C:10]=12)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 58123592HCID 58123592, compound

Product 1

HCID 66942140HCID 66942140, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (2R,6S)-3-benzyl-6,11,11-trimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo-[d]azocine-10-carboxylic acid ethyl ester (0.96 g) in tetrahydrofuran (2 mL) is added dropwise to LiAlH4 (1.6 mL, 2.4 mol/L in THF) in tetrahydrofuran (1.5 mL). The reaction mixture is stirred at ambient temperature for 90 min. Then, water (4 mL) is added carefully and the resulting mixture is extracted with ethyl acetate. The combined organic extracts are washed with water and brine and dried (MgSO4). The solvent is removed under reduced pressure to give the product.

Workup

  1. extractionthe resulting mixture is extracted with ethyl acetate
  2. washThe combined organic extracts are washed with water and brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent is removed under reduced pressure
  5. customto give the product

Sources & evidence

ORD record
ord-b24609b1d0af477196293109442defa5
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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